Enterprise Renewals Executive
$200,000 USD/year Pay is set based on global value, not the local market. Most roles = hourly rate x 40 hrs x 50 weeks 

Worldwide
Semi-flexible schedule
Fully-remote
full-time (40 hrs/week)
Long-term role

Enterprise Renewals Executive   $200,000 USD/year

Description

If you're a seasoned enterprise sales or customer success professional who excels in high-stakes negotiations, values direct engagement with senior executives, and is ready to master AI-enhanced sales execution, this opportunity is designed for you. You'll take full ownership of the renewals pipeline for high-value enterprise accounts, lead conversations directly with decision-makers, and close multi-million-dollar contracts.

Trilogy is not a conventional SaaS sales organization built on arbitrary quotas, commission structures, or excessive management layers. We are an AI-first company fundamentally transforming enterprise sales: streamlining deal execution, refining risk assessment, and enhancing stakeholder engagement through AI-powered insights. You'll join a team that operates with speed, iterates relentlessly, and uses AI to remove inefficiencies—freeing you to concentrate on activities that close deals. Rather than chasing commissions, you'll benefit from the predictability of a guaranteed compensation plan, enabling you to refine your sales expertise without the uncertainty of variable payouts.

This is not an oversight role where you sit back and monitor renewals. It's a hands-on, execution-focused position requiring you to manage a renewals pipeline, pinpoint key economic buyers, address objections, and drive contract renewals with precision. You won't be managing a team or losing time in endless internal meetings. You'll be directly engaged, negotiating high-value renewals and securing long-term customer retention.

If you're ready to shape the future of AI-driven sales while taking ownership of high-impact deals, apply now!

What you will be doing

  • Drive high-touch engagements with key customers, ensuring alignment on value, addressing objections, and securing renewals
  • Develop and continuously refine structured B2B renewals playbooks, AI-enhanced sales strategies, and frameworks designed to maximize retention and revenue

What you will NOT be doing

  • Pursuing new logo sales or prospecting for new leads
  • Processing high-volume, low-value renewals

Key responsibilities

  • Take full ownership of the renewals process for high-value enterprise accounts, acting as the primary point of contact with the objective of retaining revenue and reducing churn

Candidate requirements

  • 8+ years of experience in a CSM or account management role at a software/SaaS/Cloud products company serving Enterprise clients
  • Experience managing the entire renewal cycle — client engagement, value proposition, negotiation, managing paper process, and closing deals worth $100K+
  • Fluent English, with strong verbal and written proficiency
  • Experience using AI tools in a professional setting
  • Must be able to work during U.S. business hours

Nice to have

  • Proven track record renewing complex, high-value B2B software (SaaS and on-prem) and related services with large enterprises
  • Experience selling multiple products across different verticals or business units
  • Comfort selling value-added services and premium tiers based on business benefit rather than price
  • Hands-on use of ChatGPT or Claude to enhance the quality and throughput of customer-facing work

Meet a successful candidate

Watch Interview
Najeeha Humayun
Najeeha  |  AI-First Strategic Sales Specialist
Switzerland

Who says you have to choose between building a family and building an epic career? Najeeha didn’t. After pivoting from finance to tech, she ...

Meet Najeeha

Applying for a role? Here’s what to expect.

Crossover's skill assessment process combines innovative AI power with decades of human research, to take the guesswork, human bias, and pointless filters out of recruiting high-performing teams.

Chat-style
screening interview.
STEP 1

Chat-style
screening interview.

Cognitive 
aptitude test.
STEP 2

Cognitive 
aptitude test.

Prove real-world 
job skills.
STEP 3

Prove real-world 
job skills.

Interview with the hiring manager.
STEP 4

Interview with the hiring manager.

Pass
proctored test.
STEP 5

Pass
proctored test.

Accept job offer.
STEP 6

Accept job offer.

Frequently asked questions

About Crossover

Meet some people who've landed similar jobs

Why Crossover

School sucks. So we’re fixing it.

The education Olympics

The education Olympics

It’s hard to qualify – on purpose. High standards mean every educator, leader and EdTech builder is at the top of their game. 

Salary without side gigs

Salary without side gigs

Top performers earn what they’re worth. Six-figure education roles aren’t fantasy here – they’re the baseline for excellence.

Skills make the grade

Skills make the grade

Skills carry more weight that resumes here. Demonstrate learning mastery, AI fluency and passion for what’s next. That’s what counts.

Crossover Logo White
Follow us on
Have a question?

Get answers to common questions using our smart chatbot Crosby.

HELP AND FAQs

Join America’s largest community of  AI first education leadersAI-first education leaders.